Startup Resources

When you find an ideal freelancer for your business, you want him or her to see your future projects as something to get excited about. These tips can help you build a long-term relationship with someone who works with you on a contract basis.

Freelancers value not being tied down. According to a study by IBM, flexibility is the number-one factor in the decision to become an independent contractor, followed closely by the ability to be their own boss. Recognizing these priorities as you work together will help ensure your freelancers value you as a top client—one they’re eager to work for repeatedly—and so will the following suggestions.

Begin With a Proper Onboarding Process

Onboarding isn’t just for staff; a good freelancer onboarding process can help independent contractors contribute more effectively.

Your onboarding process should set freelancers up with project specifications, clear expectations, and access to relevant systems, applications, or file shares. Review their invoicing process and connect them with the appropriate contact for accounts payable so he or she can get paid easily and on time. In addition, onboarding helps to introduce freelancers—if not in person then via video chat, phone, or email—to others involved in the project.

Brief freelancers not just on their project but also on your company, brand, audience, and mission statement. This sort of onboarding provides context for the work they’ll be doing, which can only help the end result. Just as important, it shows that you value the freelancers enough to invest time in them. This in turn will help humanize you, and by default your company; people relate better to other people than to a faceless organization.

Be Accessible

No matter how detailed your project brief and how thorough your onboarding, freelancers may still have questions or concerns. From the get-go, provide an email address and/or a phone number where they can reach you. If they do get in touch, respond promptly—even if it’s just to say that you don’t have the answer but are working on getting it.

Don’t Micromanage

It’s fine to touch base regularly with a freelancer who’s working for you on an extended project so you can discuss goals, timelines, potential snafus, and the like. But dictating the specifics of how they meet those goals and deadlines will get you in trouble.

For one thing, when it comes to independent contractors, the IRS has stated, “If you have the right to control or direct not only what is to be done, but also how it is to be done, then your workers are most likely employees” rather than freelancers. For another, as evident from the IBM study mentioned above, freelancers often go freelance because they want to be free from micromanagers and other bosses.

Provide Feedback

Given that these are freelancers you want to retain, you’re obviously pleased with their work. So let them know it. If there are aspects of the work they could improve, mention those as well, perhaps as part of what psychologists call a “praise sandwich”: Open with praise, discuss the area that could stand improvement, then conclude with overall praise.

Also praise worthy freelancers in a public forum, such as on their Upwork profile or LinkedIn page. Providing feedback shows their contributions have been noted and appreciated, and appreciation is a huge driver of loyalty.

Include Freelancers in Project Postmortems

Not only will their input prove valuable, it will help illustrate their role in the project.

Keep Freelancers Updated About Projects They Worked On

Did an article they wrote for your website receive an unprecedented number of shares? Did the CEO praise an app they created? Did a client write a letter of thanks for how they handled a customer service problem? If so, let them know—even after their project has ended. A complimentary email or phone call will help keep your company on a freelancer’s radar in a highly positive way.

Get in Touch With Freelancers Periodically Between Projects

This is especially important when your projects are seasonal. Ask a freelancer about their availability several weeks or even months before you think you’ll want to hire them again; don’t assume they’re waiting for the proverbial phone to ring.

If you haven’t had cause to use them for a longer-than-usual period of time but think you might want their services again soon, let them know. Freelancers who don’t hear from a client over time will assume that they’ll never hear from the client again—especially if they hadn’t previously received feedback from the client—and will fill their schedules with other projects. “Out of sight, out of mind” very much applies here.

Pay On Time

It’s a no-brainer but worth reiterating. Get a group of freelancers in a room, ask them about the clients they’ll never work with again, and chances are good that more than a few will gripe about companies that failed to pay them on time.

Above all, remember that freelancers are people. Find ways to recognize their work; ask how they’re doing or what they have planned for the weekend. The most effective—and easiest—way to engender engagement in people is to engage with them yourself.

Sherry Chiger

Writer and Editor

An award-winning writer and editor, Sherry Chiger was editorial director for two magazines, in the U.S. and the U.K., covering multichannel commerce. She now writes sales copy, articles, and marketing content for a variety of marketers and publications. She is the author of two nonfiction children’s books and a novel, Beyond Billicombe.